CH636116A5 - HETEROCYCLIC DISPERSION DYES. - Google Patents

HETEROCYCLIC DISPERSION DYES. Download PDF

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Publication number
CH636116A5
CH636116A5 CH815178A CH815178A CH636116A5 CH 636116 A5 CH636116 A5 CH 636116A5 CH 815178 A CH815178 A CH 815178A CH 815178 A CH815178 A CH 815178A CH 636116 A5 CH636116 A5 CH 636116A5
Authority
CH
Switzerland
Prior art keywords
formula
alkoxy
parts
dyes
alkyl
Prior art date
Application number
CH815178A
Other languages
German (de)
Inventor
Werner Dr Baumann
Original Assignee
Sandoz Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH815178A priority Critical patent/CH636116A5/en
Priority to FR7918579A priority patent/FR2438045A1/en
Priority to DE2929001A priority patent/DE2929001C2/en
Priority to DE19792954436 priority patent/DE2954436C2/de
Priority to IT49814/79A priority patent/IT1162353B/en
Priority to GB8133975A priority patent/GB2084153B/en
Priority to GB7925756A priority patent/GB2026528B/en
Priority to US06/060,745 priority patent/US4281115A/en
Priority to DD79214638A priority patent/DD145110A5/en
Priority to YU1832/79A priority patent/YU40066B/en
Priority to BE0/196480A priority patent/BE877921A/en
Priority to CA000332603A priority patent/CA1140551A/en
Priority to JP9595979A priority patent/JPS5534288A/en
Priority to ZA00793851A priority patent/ZA793851B/en
Priority to BR7904834A priority patent/BR7904834A/en
Priority to AT0518779A priority patent/AT387580B/en
Priority to AR277502A priority patent/AR231993A1/en
Priority to ES482926A priority patent/ES482926A1/en
Priority to FR7932038A priority patent/FR2438655A1/en
Priority to CH679182A priority patent/CH638514A5/en
Publication of CH636116A5 publication Critical patent/CH636116A5/en
Priority to JP60015621A priority patent/JPS60186566A/en
Priority to SG106/85A priority patent/SG10685G/en
Priority to HK91/89A priority patent/HK9189A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Coloring (AREA)
  • Hydrogenated Pyridines (AREA)

Description

Gegenstand der Erfindung sind Dispersionsfarbstoffe, die eine Gruppe der Formel I The invention relates to disperse dyes which form a group of the formula I.

/ /

CN CN

NC — -CH NC - -CH

R. R.

(I) (I)

SO SO

tragensworin wearing word

R! der Rest eines Systems aromatischen Charakters ist, und ihre Herstellung, die dadurch gekennzeichnet ist, dass man eine Verbindung der Formel II R! the rest of a system is aromatic in character, and their preparation, which is characterized in that a compound of formula II

/ /

NC —C NC —C

CN CN

■,tP' ■, tP '

so' so'

R2 Wasserstoff, Chlor, Brom, Hydroxy, Amino, C^-Alkyl, Phenyl, Cx_2-Alkoxy, Phenoxy, Cyan, Nitro, C^-Alkylsulfonyl, 30 Aminosulfonyl, Mono- oder Di-C^-Alkylaminosulfonyl, Phe-nylaminosulfonyl, N-Phenyl-N-C^-alkylaminosulfonyl, C^-Alkoxy-carbonyl, Phenoxycarbonyl, Aminocarbonyl, Mono-oder Di-C^-alkyl-aminocarbonyl, Phenylaminocarbonyl oder N-Phenyl-N-C1_2-alkyl-aminocarbonyl, C^-Alkylcarbonyloxy, 35 Chlor- oder Brom-C1_2-alkylcarbonyloxy, C^-Alkoxycarbo-nyloxy, Phenoxycarbonyloxy, C^-Alkylsulfonyloxy, Phenylsul-fonyloxy, C^-Alkylcarbonylamino, C1_2-Alkoxy-CM-alkoxy-carbonylamino, Chlor- oderBrom-C1_2-alkylcarbonylamino, C^-Alkoxycarbonylamino, Phenoxycarbonylamino, Aminolo carbonylamino, Mono- oder Di-C^-alkylaminocarbonylamino, Phenylaminocarbonylamino, N-Phenyl-N-C^-alkylaminocar-bonylamino, Benzoyloxy, Naphthoyloxy, Benzoylamino, Di-C^-alkylaminosulfonyloxy, Mono- oder Di-C^-alkylamino-carbonyloxy oder Phenylaminocarbonyloxy, 4s R3 Wasserstoff, Chlor, Brom, Q^-Alkyl, Q^-AIkoxy oder Cj^-Alkoxy-carbonyl, R2 is hydrogen, chlorine, bromine, hydroxyl, amino, C ^ alkyl, phenyl, Cx_2 alkoxy, phenoxy, cyano, nitro, C ^ alkylsulfonyl, 30 aminosulfonyl, mono- or di-C ^ -alkylaminosulfonyl, phenylaminosulfonyl, N-phenyl-NC ^ -alkylaminosulfonyl, C ^ -alkoxy-carbonyl, phenoxycarbonyl, aminocarbonyl, mono- or di-C ^ -alkyl-aminocarbonyl, phenylaminocarbonyl or N-phenyl-N-C1_2-alkyl-aminocarbonyl, C ^ -alkylcarbonyloxy , 35 chloro or bromo-C1_2-alkylcarbonyloxy, C ^ -alkoxycarbo-nyloxy, phenoxycarbonyloxy, C ^ -alkylsulfonyloxy, phenylsul-fonyloxy, C ^ -alkylcarbonylamino, C1_2-alkoxy-CM-alkoxy-carbonylamino, chlorine or bromine-C1_2- alkylcarbonylamino, C ^ -alkoxycarbonylamino, phenoxycarbonylamino, aminolo carbonylamino, mono- or di-C ^ -alkylaminocarbonylamino, phenylaminocarbonylamino, N-phenyl-NC ^ -alkylaminocar-bonylamino, benzoyloxy, naphthoyloxy, benzoylamino, di-Cyl-alkyl-mono-alkyl- or di-C ^ -alkylamino-carbonyloxy or phenylaminocarbonyloxy, 4s R3 hydrogen, chlorine, bromine, Q ^ -alkyl, Q ^ -alkoxy or C j ^ alkoxy-carbonyl,

R4 Hydroxyl, C^-Alkoxy oder eine Gruppe der Formel R4 hydroxyl, C ^ alkoxy or a group of the formula

(II) (II)

50 50

-n: -n:

■r7 ■ r7

R« R «

mit einem gegebenenfalls funktionell abgewandelten Aldehyd kondensiert. Die Zwischenprodukte der obigen Formel II werden hergestellt, indem man eine Verbindung der Formel III condensed with an optionally functionally modified aldehyde. The intermediates of formula II above are prepared by using a compound of formula III

(III) (III)

mit Malonsäuredinitril kondensiert. condensed with malononitrile.

Bevorzugt sind die erfindungsgemässen Farbstoffe, worin Ri eine gegebenenfalls Substituenten tragende, einen Benzolring vervollständigende Atomgruppe ist. The dyes according to the invention are preferred, in which Ri is an atomic group which optionally carries substituents and completes a benzene ring.

R5 Wasserstoff, Hydroxyl, C^-Alkyl oder C^-Alkoxy, 55 R6 Wasserstoff, Chlor, Brom, Hydroxyl, C^-Allcyl, C^-Alkoxy, Phenoxy, Cj^-Alkylcarbonylamino, Phenylcarbonyl-amino, C^-Alkoxy-carbonylamino, Q^-Alkylcarbonyloxy, Phenylcarbonyloxy, Naphthylcarbonyloxy, Chlor- oder Brom-Q_2-alkylcarbonyloxy, C^-AIkoxycarbonyloxy, C1_2-Alkoxy-6o C2_6-alkoxy-carbonylo);y, Phenoxycarbonyloxy, C^-Alkylsul-fonyloxy, Phenylsulfonyloxy, Di-C^-allcylaminosulfonyloxy, Di-C^-Alkylaminocarbonyloxy, C^-Alkylamino-carbonyl-oxy, Phenyl, Phenylamino-carbonyloxy oder Phenoxycarbonylamino, R5 is hydrogen, hydroxyl, C ^ alkyl or C ^ alkoxy, 55 R6 hydrogen, chlorine, bromine, hydroxyl, C ^ alkylc, C ^ alkoxy, phenoxy, Cj ^ alkylcarbonylamino, phenylcarbonylamino, C ^ alkoxy -carbonylamino, Q ^ -alkylcarbonyloxy, phenylcarbonyloxy, naphthylcarbonyloxy, chloro- or bromo-Q_2-alkylcarbonyloxy, C ^ -AIkoxycarbonyloxy, C1_2-alkoxy-6o C2_6-alkoxy-carbonylo); y, phenoxycarbonyloxy, C ^ -alkylsulylsulfonyloxy , Di-C ^ -allcylaminosulfonyloxy, di-C ^ -alkylaminocarbonyloxy, C ^ -alkylamino-carbonyl-oxy, phenyl, phenylamino-carbonyloxy or phenoxycarbonylamino,

65 65

R7 und R8 unabhängig voneinander Wasserstoff, Cj,_12-A1-kyl, Benzyl, C5_7-Cycloalkyl, Allyl oder C2_g-Alkyl, das ein Chlor, Brom, Hydroxyl, C^-Alkoxy, Phenyl, Phenoxy, Cyan, C1_3-Alkoxy-carbonyl, C1_2-Alkyl-carbonyloxy, C^-Alkoxy- R7 and R8 independently of one another are hydrogen, Cj, _12-A1-kyl, benzyl, C5_7-cycloalkyl, allyl or C2_g-alkyl, which is a chlorine, bromine, hydroxyl, C ^ -alkoxy, phenyl, phenoxy, cyano, C1_3-alkoxy- carbonyl, C1_2-alkyl-carbonyloxy, C ^ -alkoxy-

3 3rd

636116 636116

carbonyloxy, Benzoyloxy oder Phenylaminocarbonyloxy tragen kann, bedeuten, wobei R5 und und/oder R5 und R7 und/oder R7 und R8 zusammen die für die Bildung eines 5- oder 6-gliedri-gen carbocyclischen resp. heterocyclischen Ringes notwendigen Atomgruppen sein können und die genannten Phenyl- und Naphthylkerne bis zu drei Substituenten tragen können, darunter bis zu zwei Chlor, Brom, Hydroxyl, C1_2-Alkyl und C^-Alkoxy und/oder ein C1_2-Alkoxy-carbonyl, Aminocarbonyl, Q-2-AlkyI- oder N,N-Di-C]_2-aIkylamino-carbonyl, Aminosul-fonyl und/oder C1_2-Alkyl- oder N,N-Di-C1_2-alkylaminosulfo-nyl. can carry carbonyloxy, benzoyloxy or phenylaminocarbonyloxy, where R5 and / or R5 and R7 and / or R7 and R8 together together for the formation of a 5- or 6-membered carbocyclic or. heterocyclic ring necessary atomic groups and the phenyl and naphthyl nuclei mentioned can carry up to three substituents, including up to two chlorine, bromine, hydroxyl, C1_2-alkyl and C ^ alkoxy and / or a C1_2-alkoxycarbonyl, aminocarbonyl, Q-2-alkyl or N, N-di-C] _2-alkylamino-carbonyl, aminosulfonyl and / or C1_2-alkyl or N, N-di-C1_2-alkylaminosulfonyl.

Die Kondensation einer Verbindung der Formel III mit Ma-lonsäuredinitril erfolgt analog zu ähnlichen Reaktionen (Knoe-venagel-Kondensation), vorzugsweise in inerten, organischen Lösungsmitteln, z.B. Alkoholen, insbesondere Äthanol, n-Pro-panol, Isopropanol, n-Butanol, Isobutanol, sec.-Butanol, tert.-Butanol, Methoxy- oder Äthoxyäthanol; ferner Benzol, Toluol, Chlorbenzol, Dichlorbenzole, Chloroform, Dimethylformamid, N-Methylpyrrolidon, Dimethylsulfoxid, Sulfolan oder Acetoni-tril, bei Temperaturen zwischen 20 und 150 °C, vorzugsweise 50-120 °C, wobei die Anwesenheit eines Katalysators, vorzugsweise einer organischen Base, z.B. Pyridin, Piperidin oder ein Gemisch aus Piperidin und Eisessig, von Vorteil ist. The condensation of a compound of formula III with malononitrile is carried out analogously to similar reactions (Knoe venagel condensation), preferably in inert, organic solvents, e.g. Alcohols, especially ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol, methoxy or ethoxy ethanol; further benzene, toluene, chlorobenzene, dichlorobenzenes, chloroform, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane or acetonitrile, at temperatures between 20 and 150 ° C, preferably 50-120 ° C, the presence of a catalyst, preferably an organic Base, e.g. Pyridine, piperidine or a mixture of piperidine and glacial acetic acid is an advantage.

Die Kondensation der erhaltenen Verbindung der Formel II mit dem gegebenenfalls funktionell abgewandelten Aldehyd findet unter ähnlichen Bedingungen statt. The condensation of the compound of formula II obtained with the optionally functionally modified aldehyde takes place under similar conditions.

Die Verbindungen der Formel III sind bekannt oder lassen sich leicht analog zu den bekannten Herstellungsverfahren synthetisieren. The compounds of formula III are known or can be easily synthesized analogously to the known production processes.

Die neuen Farbstoffe zeichnen sich insbesondere durch ihre hervorragende Brillanz und Farbstärke aus und besitzen sehr gute Allgemeinechtheiten. The new dyes are particularly characterized by their excellent brilliance and color strength and have very good general fastness properties.

Die Verarbeitung der neuen Dispersionsfarbstoffe zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z.B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken. Die Farbstoffe ziehen aus wässri-ger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben, Klotzen oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus Cellulose-2'/2-acetat, Celluloseacetat und synthetischen Polyamiden. The processing of the new disperse dyes into dyeing preparations is carried out in a generally known manner, e.g. by grinding in the presence of dispersants and / or fillers. With the preparations which may have been dried in vacuo or by atomization, after adding more or less water, it is possible to dye, pad or print in a so-called long or short liquor. The dyes are excellently absorbed from aqueous suspensions on textile material made from fully synthetic or semi-synthetic, hydrophobic, high-molecular organic substances. They are particularly suitable for dyeing, padding or printing textile materials made from linear, aromatic polyesters, as well as from cellulose 2 '/ 2-acetate, cellulose acetate and synthetic polyamides.

Man färbt, klotzt oder bedruckt nach an sich bekannten, z.B. dem in der französischen Patentschrift Nr. 1 445 371 beschriebenen Verfahren oder nach einem der bekannten Lö-sungsmittel-Färbeverfahren. Dyeing, padding or printing according to known, e.g. the process described in French Patent No. 1,445,371 or by one of the known solvent dyeing processes.

Häufig ist es möglich, die Farbstoffe durch eine Wärme-, Lösungsmittel- und/oder Mahlbehandlung oder durch Umkri-stallisation in eine andere, stabile Modifikation überzuführen. Geeignete Methoden und die dabei erzielbaren Vorteile sind dem Fachmann bekannt. It is often possible to convert the dyes into another, stable modification by heat, solvent and / or grinding treatment or by recrystallization. Suitable methods and the advantages that can be achieved are known to the person skilled in the art.

In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente; die Temperaturen sind in Celsiusgraden angegeben. In the following examples, parts are parts by weight and percentages are percentages by weight; the temperatures are given in degrees Celsius.

noi gelöst und unter Rühren 6 Stunden auf 60° erwärmt, mit weiteren 4 Teilen Malonsäuredinitril versetzt und weitere 16 Stunden bei 60° gerührt. Hierauf wird das Gemisch auf 5° abgekühlt und das auskristallisierte Produkt der Formel noi dissolved and heated to 60 ° for 6 hours with stirring, a further 4 parts of malononitrile were added and the mixture was stirred at 60 ° for a further 16 hours. The mixture is then cooled to 5 ° and the crystallized product of the formula

10 10th

15 abfiltriert, mit eiskaltem Äthanol gewaschen und unter Vakuum getrocknet. 15 filtered off, washed with ice-cold ethanol and dried under vacuum.

b) 10 Teile der gemäss a) erhaltenen Verbindung werden mit 7,7 Teilen 4-Diäthylamino-benzaldehyd und 0,1 Teil einer Mischung (1:5) aus Piperidin und Eisessig in 100 Teilen absolu-20 tem Alkohol 2 Stunden unter Rückfluss gekocht. Nach dem Abkühlen auf 5° wird der auskristallisierte Farbstoff der Formel b) 10 parts of the compound obtained according to a) are refluxed with 7.7 parts of 4-diethylamino-benzaldehyde and 0.1 part of a mixture (1: 5) of piperidine and glacial acetic acid in 100 parts of absolute alcohol for 2 hours . After cooling to 5 °, the crystallized dye of the formula

25 25th

30 30th

/ /

CN CN

Wi " Wi "

NC—C ,—, NC — C, -,

35 35

40 40

45 45

50 50

abfiltriert, mit eiskaltem, absolutem Äthanol gewaschen und unter Vakuum getrocknet. filtered off, washed with ice-cold, absolute ethanol and dried under vacuum.

Färbebeispiel Coloring example

7 Teile des gemäss Beispiel 1 erhaltenen Farbstoffs werden mit 13 Teilen ligninsulfonsaurem Natrium, 25 Teilen Wasser und 100 Teilen Siliquarzitperlen gemahlen, bis der Durchmesser der Farbstoffteilchen im Mittel unter 1 (i liegt. Die Suspension wird von den Siliquarzitperlen abfiltriert und unter milden Bedingungen getrocknet und zerstäubt. 1 Teil des so erhaltenen Farbstoffpräparates wird mit 4000 Teilen 60° warmem, auf pH 5 abgepuffertem Wasser verrührt. Mit dieser Färbeflotte werden 100 Teile Polyesterfasergewebe unter Zugabe von 20 Teilen ortho-Phenylphenol 1 Stunde bei 98° gefärbt. Nach dem Abkühlen, Spülen, Seifen, nochmaligem Spülen und Trocknen erhält man eine ausserordentliche brillante, egale blaue Färbung von hohem Echtheitsniveau. 7 parts of the dye obtained according to Example 1 are ground with 13 parts of sodium lignosulfonate, 25 parts of water and 100 parts of silica quartz beads until the diameter of the dye particles is below 1 (i). The suspension of the silica quartz beads is filtered off and dried under mild conditions and 1 part of the dye preparation thus obtained is stirred with 4000 parts of warm water at 60 ° C., buffered to pH 5. 100 parts of polyester fiber fabric are dyed with this dyeing liquor with the addition of 20 parts of ortho-phenylphenol at 98 ° C. After cooling, rinsing , Soaps, repeated rinsing and drying results in an extraordinarily brilliant, level blue color of a high level of authenticity.

In der folgenden Tabelle sind weitere, analog zur Arbeitsvorschrift des Beispiels 1 hergestellte Farbstoffe der Formel The following table shows further dyes of the formula prepared analogously to the working procedure of Example 1

55 55

R. R.

7\ 7 \

CN CN

t t

NC- n NC- n

R R

N N

R, R,

65 65

Beispiel 1 example 1

a) 20 Teile 3-Oxo-2,3-dihydro-benzothiophen-l,l-dioxid, 8 Teile Malonsäuredinitril und 0,2 Teile einer Mischung (1:5) aus angegeben, die alle, auf Polyestermaterial ausgefärbt, Färbun-Piperidin und Eisessig werden in 250 Teilen wasserfreiem Ätha- gen blauer Nuancen liefern. a) 20 parts of 3-oxo-2,3-dihydro-benzothiophene-l, l-dioxide, 8 parts of malononitrile and 0.2 part of a mixture (1: 5) from, all of which are colored on polyester material, dyeing-piperidine and glacial acetic acid will deliver blue nuances in 250 parts of anhydrous ether.

2 2nd

3 3rd

4 4th

5 5

6 6

7 7

8 8th

9 9

10 10th

11 11

12 12

13 13

14 14

15 15

16 16

17 17th

18 18th

19 19th

20 20th

21 21st

22 22

23 23

24 24th

25 25th

26 26

27 27th

28 28

Re R7 Re R7

h h " h h "

-ch3 -ch3

-ch3 -ch3

h H

2-ch3 2-ch3

-C2H5 -C2H5

-q>h5 -q> h5

h H

2-c1 2-c1

do. do.

do. do.

h H

2-och3 2-och3

do. do.

do. do.

5'-cl 5'-cl

2-ch3 2-ch3

do. do.

do. do.

6'-cl do. 6'-cl do.

do. do.

do. do.

5'-ch3 5'-ch3

do. do.

do. do.

do. do.

6'-ch3 6'-ch3

do. do.

do. do.

do. do.

5'-och3 5'-och3

do. do.

do. do.

do. do.

6'-och3 6'-och3

do. do.

do. do.

do. do.

h do. h do.

do. do.

-ch2-c6h5 -ch2-c6h5

h do. h do.

do. do.

-ch2ch2-ci h -ch2ch2-ci h

do. do.

do. do.

-ch2ch2-cn h -ch2ch2-cn h

do. do.

do. do.

-ch2ch2-oh h -ch2ch2-oh h

do. do.

do. do.

-ch2ch2-o-coch3 -ch2ch2-o-coch3

h do. h do.

do. do.

-ch2ch2-o-co-nh- -ch2ch2-o-co-nh-

h do. h do.

do. do.

-ch2ch2-o-co-nh h -ch2ch2-o-co-nh h

do. do.

-c4h9 -c4h9

-C2H5 -C2H5

.Cl .Cl

H do. do. -CH2CH2OH H do. do. -CH2CH2OH

H do. do. -CH2CH2-0-C0-NH-C6H5 H do. do. -CH2CH2-0-C0-NH-C6H5

30 CI 30 CI

H do. do. -CH2CH2-0-C0-NH -©-CI H do. do. -CH2CH2-0-C0-NH - © -CI

5'-Cl do. do. do. 5'-Cl do. do. do.

6'-Cl do. do. do. 6'-Cl do. do. do.

5'-CI do. -C2H5 -CH2CH2-0-C0-NH-C6H5 5'-CI do. -C2H5 -CH2CH2-0-C0-NH-C6H5

6'-Cl do. do. do. 6'-Cl do. do. do.

H do. -(CH2)5- H do. - (CH2) 5-

H do. -CH2CH2-0-CH2CH2- H do. -CH2CH2-0-CH2CH2-

Claims (2)

636116 636116 PATENTANSPRÜCHE 1. Dispersionsfarbstoffe, die eine Gruppe der Formel I PATENT CLAIMS 1. Disperse dyes that form a group of formula I Besonders bevorzugt sind die Dispersionsfarbstoffe der Formel I a The disperse dyes of the formula I a are particularly preferred / / NC--G NC - G -CH=* -CH = * CN CN R R / / nc — g nc - g Cw Cw R. R. (I) (I) SO, SO, ch' ch ' (Ia), (Ia), SO, SO, 10 10th tragen,worin wear what Rj der Rest eines Systems aromatischen Charakters ist. 2. Verfahren zur Herstellung der Farbstoffe gemäss Anspruch 1, dadurch gekennzeichnet, dass man eine Verbindung der Formel II Rj is the remainder of an aromatic system. 2. A process for the preparation of the dyes according to claim 1, characterized in that a compound of formula II worin der Ring A mindestens einen auxochromen Substituenten enthält und gegebenenfalls weitere Substituenten trägt und/ oder an einen weiteren Ring anelliert ist. wherein the ring A contains at least one auxochromic substituent and optionally carries further substituents and / or is fused to a further ring. Insbesondere bevorzugt sind die Dispersionsfarbstoffe der 15 Formel Ib The disperse dyes of the formula Ib are particularly preferred 20 20th (II) R, (II) R, mit einem gegebenenfalls funktionell abgewandelten Aldehyd 25 kondensiert. condensed with an optionally functionally modified aldehyde 25. (Ib), (Ib), R, R, worin wherein
CH815178A 1978-07-28 1978-07-28 HETEROCYCLIC DISPERSION DYES. CH636116A5 (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
CH815178A CH636116A5 (en) 1978-07-28 1978-07-28 HETEROCYCLIC DISPERSION DYES.
FR7918579A FR2438045A1 (en) 1978-07-28 1979-07-18 NOVEL 3-DICYANOMETHYLIDENE-2,3-DIHYDRO-THIOPHENE-1,1-DIOXYDES, THEIR PREPARATION AND THEIR USE AS DYES
DE2929001A DE2929001C2 (en) 1978-07-28 1979-07-18 Disperse dyes and process for their preparation
DE19792954436 DE2954436C2 (en) 1978-07-28 1979-07-18
IT49814/79A IT1162353B (en) 1978-07-28 1979-07-20 3-DIANANOMETILIDEN-2,3-DIIDRO-TIOFEN-1,1-DIOXIDES THEIR PREPARATION AND THEIR USE AS DYES
GB8133975A GB2084153B (en) 1978-07-28 1979-07-24 Dicyanomethylidene-dihydrothiophene dioxide derivatives
GB7925756A GB2026528B (en) 1978-07-28 1979-07-24 Organic compounds
US06/060,745 US4281115A (en) 1978-07-28 1979-07-25 3-Dicyanomethylidene-2,3-dihydrothiophen-1,1-dioxide derivatives
CA000332603A CA1140551A (en) 1978-07-28 1979-07-26 3,3-dicyanomethylidene-2,3-dihydrothiophen -1,1-dioxide derivatives
YU1832/79A YU40066B (en) 1978-07-28 1979-07-26 Process for preparing dispersion dyes with a 3-dicayanomethylene-2,3-dihdro-benzothiophene-1,1-dioxide chromophore
BE0/196480A BE877921A (en) 1978-07-28 1979-07-26 NOVEL 3-DICYANOMETHYLIDENE-2,3-DIHYDROTHIOPHENE-1,1-DIOXIDES, THEIR PREPARATION AND THEIR USE AS DYES
DD79214638A DD145110A5 (en) 1978-07-28 1979-07-26 PROCESS FOR PREPARING DISPERSION DYES
AT0518779A AT387580B (en) 1978-07-28 1979-07-27 METHOD FOR PRODUCING DISPERSION DYES
ZA00793851A ZA793851B (en) 1978-07-28 1979-07-27 Disperse dyestuffs
BR7904834A BR7904834A (en) 1978-07-28 1979-07-27 PROCESS FOR THE PRODUCTION OF A COMPOUND, PROCESS FOR THE PRODUCTION OF AN INTERMEDIATE FOR THE SAME, AND PROCESS FOR DYEING OR STAMPING OF TEXTILES APPLYING THAT COMPOUND
JP9595979A JPS5534288A (en) 1978-07-28 1979-07-27 Dispersion dyestuff
AR277502A AR231993A1 (en) 1978-07-28 1979-07-27 DISPERSION DYES FOR DICLANO-METHYLIDEN-2,3-DIHYDROTIOPHENE 1,1-DIOXIDE, PROCEDURE FOR OBTAINING THEM, COMPOUNDS OF 3- (DICIANOMETILIDEN) -2.3 DIHYDROBENZOTHIOPHENE FOR EXCLUSIVE APPLICATION IN THAT PROCEDURE AND PROCEDURE
ES482926A ES482926A1 (en) 1978-07-28 1979-07-27 3-Dicyanomethylidene-2,3-dihydrothiophen-1,1-dioxide derivatives
FR7932038A FR2438655A1 (en) 1978-07-28 1979-12-28 NOVEL 3-DICYANOMETHYLIDENE-2,3-DIHYDRO-THIOPENE-1,1-DIOXIDES CONDENSES AND THEIR PREPARATION
CH679182A CH638514A5 (en) 1978-07-28 1982-11-22 ARYLTHIOPHENEDIOXIDE COMPOUNDS.
JP60015621A JPS60186566A (en) 1978-07-28 1985-01-31 Dicyanomethylidene-dihydrothiophene dioxide de rivative
SG106/85A SG10685G (en) 1978-07-28 1985-02-08 Dicyanomethylidene-dihydrothiophene dioxide derivatives
HK91/89A HK9189A (en) 1978-07-28 1989-02-02 Dicyanomethylidene-dihydro-thiophene dioxide derivatives

Applications Claiming Priority (1)

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CH815178A CH636116A5 (en) 1978-07-28 1978-07-28 HETEROCYCLIC DISPERSION DYES.

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CH679182A CH638514A5 (en) 1978-07-28 1982-11-22 ARYLTHIOPHENEDIOXIDE COMPOUNDS.

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Country Status (18)

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US (1) US4281115A (en)
JP (2) JPS5534288A (en)
AR (1) AR231993A1 (en)
AT (1) AT387580B (en)
BE (1) BE877921A (en)
BR (1) BR7904834A (en)
CA (1) CA1140551A (en)
CH (2) CH636116A5 (en)
DD (1) DD145110A5 (en)
DE (1) DE2929001C2 (en)
ES (1) ES482926A1 (en)
FR (2) FR2438045A1 (en)
GB (2) GB2084153B (en)
HK (1) HK9189A (en)
IT (1) IT1162353B (en)
SG (1) SG10685G (en)
YU (1) YU40066B (en)
ZA (1) ZA793851B (en)

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US4750228A (en) * 1986-08-06 1988-06-14 Ciba-Geigy Corporation Disperse dyes
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US5028708A (en) * 1987-04-14 1991-07-02 Sumitomo Chemical Company, Limited Azamethinyl quinoline derivatives
US5220027A (en) * 1987-04-14 1993-06-15 Sumitomo Chemical Company, Limited Sulfone-containing azamethide compounds with a nitrogen-containing aromatic ring of nitrogen containing aliphatic
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JPH0269385U (en) * 1988-11-16 1990-05-25
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CN106675082B (en) * 2016-12-08 2019-04-05 江苏道博化工有限公司 A method of preparing disperse blue 354
CN109233323B (en) * 2018-10-25 2020-10-09 浙江闰土研究院有限公司 Preparation method of disperse blue 354
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Also Published As

Publication number Publication date
GB2084153A (en) 1982-04-07
GB2026528A (en) 1980-02-06
US4281115A (en) 1981-07-28
IT1162353B (en) 1987-03-25
ES482926A1 (en) 1980-09-01
FR2438655B1 (en) 1983-04-08
JPS632988B2 (en) 1988-01-21
JPS5534288A (en) 1980-03-10
CH638514A5 (en) 1983-09-30
FR2438045A1 (en) 1980-04-30
AT387580B (en) 1989-02-10
SG10685G (en) 1985-08-08
YU183279A (en) 1983-09-30
FR2438655A1 (en) 1980-05-09
GB2026528B (en) 1982-12-15
CA1140551A (en) 1983-02-01
BE877921A (en) 1980-01-28
YU40066B (en) 1985-06-30
DD145110A5 (en) 1980-11-19
FR2438045B1 (en) 1982-10-29
HK9189A (en) 1989-02-10
GB2084153B (en) 1983-04-07
ZA793851B (en) 1981-02-25
DE2929001A1 (en) 1980-02-14
DE2929001C2 (en) 1985-08-14
JPS60186566A (en) 1985-09-24
AR231993A1 (en) 1985-04-30
BR7904834A (en) 1980-07-08
IT7949814A0 (en) 1979-07-20
ATA518779A (en) 1988-07-15
JPS615501B2 (en) 1986-02-19

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